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Coenzyme A

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Identification
Molecular formula
C21H36N7O16P3S
CAS number
85-61-0
IUPAC name
S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 4-(7,12-dihydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pentanethioate
State
State

At room temperature, coenzyme A is typically found in solid form, especially when isolated as a powdered substance.

Melting point (Celsius)
189.00
Melting point (Kelvin)
462.15
Boiling point (Celsius)
252.00
Boiling point (Kelvin)
525.15
General information
Molecular weight
767.54g/mol
Molar mass
767.5350g/mol
Density
1.3440g/cm3
Appearence

Coenzyme A typically appears as a white or off-white powder. It is an important biochemical compound that can also be hydrated, which may affect its appearance slightly depending on its state of hydration.

Comment on solubility

Solubility of S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 4-(7,12-dihydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pentanethioate

The solubility of this complex compound, denoted by the chemical formula C21H36N7O16P3S, is influenced by several factors due to its intricate molecular structure. Here are key considerations regarding its solubility:

  • Polarity: The presence of multiple functional groups such as hydroxyls (-OH) and phosphonate groups (-PO3H2) contributes to its overall polarity, which typically enhances solubility in polar solvents, particularly water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvent molecules increases solubility. The large number of hydroxyl and amino groups in this compound facilitates extensive hydrogen bonding, enhancing solubility in aqueous environments.
  • Chain Length: The presence of long hydrocarbon chains or bulky groups can affect solubility. While some regions of this compound may be hydrophobic, the functional groups likely increase solubility in polar solvents despite such hydrophobic characteristics.
  • pH Dependency: Solubility can also vary with pH, especially for compounds containing acidic or basic functional groups. It is crucial to test solubility at various pH levels to ascertain stability.

In summary, this compound exhibits varying solubility characteristics due to its complex structure and the presence of hydrophilic functional groups. One might expect it to be soluble in polar solvents such as water, particularly under conditions that favor hydrogen bonding and lower pH levels. Understanding these aspects is pivotal when considering the practical applications and interactions of the compound in biochemical systems.

Interesting facts

Interesting Facts about S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 4-(7,12-dihydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pentanethioate

This complex compound is a fascinating example of synthetic organic chemistry, showcasing the intricate combinations of various functional groups that enable its specific biological activity. Here are some noteworthy points:

  • Component Breakdown: The structure contains multiple functional groups, including phosphoryl, amino, and thioate components, which contribute to its potential effectiveness in biochemical interactions.
  • Biological Relevance: Compounds with structural elements like purines and hydroxyl groups are often linked to biological processes, especially in the context of nucleic acids and energy metabolism, adding to the interest of this compound in pharmacological research.
  • Synthetic Challenge: The synthesis of such a compound likely involves multiple steps, dealing with challenges such as sterics, regioselectivity, and yields – making it a point of discussion in advanced organic chemistry classes.
  • Potential Applications: Due to its complexity, this compound may hold potential in drug discovery, particularly in targeting pathways involved in cancer or metabolic diseases, given the structural motifs related to known drug activity.
  • Research Interest: Scientists are continually investigating similar compounds' interactions within biological systems, contributing to the field of medicinal chemistry and pharmacology.

This compound serves as a reminder of the beautiful complexity found in biochemical substances, highlighting the ongoing dialogue between synthetic chemistry and therapeutic innovation.


Synonyms
3-oxo-cholyl-CoA; (Acyl-CoA); [M+H]+;